Defluorinated sparfloxacin as a new photoproduct identified by liquid chromatography coupled with UV detection and tandem mass spectrometry

被引:26
作者
Engler, M
Rüsing, G
Sörgel, F
Holzgrabe, U
机构
[1] Univ Bonn, Inst Pharmazeut, D-53115 Bonn, Germany
[2] Inst Biomed & Pharmaceut Res, D-90562 Nurnberg, Germany
关键词
D O I
10.1128/AAC.42.5.1151
中图分类号
Q93 [微生物学];
学科分类号
071005 ; 100705 ;
摘要
Photodegradation of sparfloxacin was observed by means of high-pressure liquid chromatography with UV detection and liquid chromatography coupled with UV detection and tandem mass spectrometry (LC-MS/MS). Three products were detected. Comparison with an independently synthesized derivative of sparfloxacin revealed the structure of one product which is believed to be 8-desfluorosparfloxacin. The second product is likely to be formed by the splitting off of a fluorine and a cyclopropyl ring. Thus, photodefluorination of quinolone antibacterial agents is found and proved for the first time by LC-MS/MS.
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页码:1151 / 1159
页数:9
相关论文
共 18 条
[1]   PHOTOCHEMISTRY OF HETEROCYCLIC ENONES .1. PHOTOLYSIS AND THERMOLYSIS OF NALIDIXIC-ACID [J].
DETZER, N ;
HUBER, B .
TETRAHEDRON, 1975, 31 (16) :1937-1941
[2]  
ENGLER M, 1996, AM CHEM SOC 2, V211
[3]   Syntheses and biological activities of new N-1-aryl substituted quinolone antibacterials [J].
Jurgens, J ;
Schedletzky, H ;
Heisig, P ;
Seydel, JK ;
Wiedemann, B ;
Holzgrabe, U .
ARCHIV DER PHARMAZIE, 1996, 329 (04) :179-190
[4]  
KAMIDE MDR, 1993, FRONTIERS PHOTOBIOLO
[5]   Photogeneration of fluoride by the fluoroquinolone antimicrobial agents lomefloxacin and fleroxacin [J].
Martinez, LJ ;
Li, G ;
Chignell, CF .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1997, 65 (03) :599-602
[6]   PHOTOSTABILITY AND BIOLOGICAL-ACTIVITY OF FLUOROQUINOLONES SUBSTITUTED AT THE 8-POSITION AFTER UV IRRADIATION [J].
MATSUMOTO, M ;
KOJIMA, K ;
NAGANO, H ;
MATSUBARA, S ;
YOKOTA, T .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1992, 36 (08) :1715-1719
[7]   PHOTOSENSITIZATION BY DRUGS - NALIDIXIC AND OXOLINIC ACIDS [J].
MOORE, DE ;
HEMMENS, VJ ;
YIP, H .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1984, 39 (01) :57-61
[8]  
MORIMURA T, 1995, CHEM PHARM BULL, V43, P1000
[9]   THE LOSS OF ANTIBIOTIC-ACTIVITY OF CIPROFLOXACIN BY PHOTODEGRADATION [J].
PHILLIPS, G ;
JOHNSON, BE ;
FERGUSON, J .
JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 1990, 26 (06) :783-789
[10]   NEW 8-(TRIFLUOROMETHYL)-SUBSTITUTED QUINOLONES - THE BENEFITS OF THE 8-FLUORO GROUP WITH REDUCED PHOTOTOXIC RISK [J].
SANCHEZ, JP ;
BRIDGES, AJ ;
BUCSH, R ;
DOMAGALA, JM ;
GOGLIOTTI, RD ;
HAGEN, SE ;
HEIFETZ, CL ;
JOANNIDES, ET ;
SESNIE, JC ;
SHAPIRO, MA ;
SZOTEK, DL .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (02) :361-367